Water → 4-(6-Hydroxy-3-methylquinolin-2-yl)benzoic acid

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Reaction Steps

Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate (37 mg, 0.121 mmol) was dissolved in 2 mL of DCM and BBr3 (150 μL) was added. The mixture was stirred at room temperature for 1 day followed by addition of 10 mL of H2O. The solution was stirred vigorously for 1 h followed by filtration of the solids. The solids were washed with H2O and dried in vacuo to yield 9.5 mg (28% yield) of Compound 1. 1H NMR (DMSO-d6, 400 MHz): δ 8.37 (s, 1H), 8.10 (d, 2H), 7.94 (d, 1H), 7.78 (d, 2H), 7.42-7.39 (dd, 1H), 7.24-7.23 (d, 1H), 2.43 (s, 3H). MS (ESI): m/z 280.10 [M+H]+.

Provenance & Evidence